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Full text of "Preliminary tests with certain m_-nitrobenzamides for synergistic action in allethrin fly sprays"

1_ 

STA 



March 1952 E-837 

United States Department of Agriculture 

Agricultural Research Administration 

Bureau of Entomology and Plant Quarantine 



PRELIMINARY TESTS WITH CERTAIN m-NITROBENZAMIDES 
FOR SYNERGISTIC ACTION IN ALLETHRIN FLY SPRAYS 

By S. I. Gertler i/ W. A. Gersdorff,-' and Norman Mitlini-' 



In previous publications in this series (E-805, E-828) the authors 
reported that certain N-substituted benzenesulfonamides and certain 
N-substituted benzamides had been found to show promise as synergists 
for pyrethrum fly sprays. In further research the action of certain 
m-nitrobenzamides in mixtures with allethrin, a synthetic insecticide, 
was examined for synergistic effect. These compounds are characterized 
by the general formula 

NOo 

\! v o / 

OK, 

R and R' cover a wide range of chemical groups. All the compounds 
were prepared by reacting m-nitrobenzoyl chloride with various amines 
under suitable conditions. 

The compounds were incorporated in sprays alone and in mixtures 
with 0.5 mg. of allethrin per milliliter. Since their solubility in refined 
kerosene was low, an equal amount of acetone was used as an auxiliary 
solvent. With one exception the concentration of the adjuncts was 20 mg. 
per milliliter. Allethrin standards were also prepared in the same 
solvent mixture at concentrations of 0.5 and 1 mg. per milliliter. The 
allethrin used in all tests was from a distilled sample of high purity. 

The tests were made by the Campbell turntable method on adult 
house flies (Musca domestica L.) reared by standard laboratory pro- 
cedure. Since knock-down is increased by the addition of acetone, it 
was not estimated. Mortality only was determined for each spray. 



1/ With the Division of Insecticide Investigations. 

2/ With the Division of Stored Product Insect Investigations, formerly 
the Division of Control Investigations. 



- 2 - 

Approximately 100 flies averaging 2 days of age were used in each test. 
The mixed sprays were replicated four times, the sprays containing the 
adjuncts alone but twice. Since it was necessary to make the tests in a 
number of series, the two standard allethrin sprays were included in 
each series as a base of reference. 

To avoid reporting many series and to put the results on a comparable 
basis, the following procedure was used: The mortalities obtained for 
the standard sprays in each series were plotted on log-probability paper 
and straight lines were drawn. From these lines the allethrin equivalents 
for the mixed sprays were estimated. Since these figures are all com- 
pared with the concentration of 0.5 mg. of allethrin per milliliter, they 
give, when multiplied by 2, expressions of relative toxicity. These 
results are assembled in table 1. Estimates of the increase in the mean 
equivalents required to show significant increase in toxicity were made 
by an analysis of variance of the logarithms of the individual equivalents. 

At the concentrations used, the adjuncts alone showed negligible 
mortality. For 10 of the mixtures the increase in toxicity was significant. 
Synergism was therefore shown in the mixtures. The effective adjuncts 
are as follows: 

N,N-Dibutyl-m-nitrobenzamide 
N,N-Diethyl-m-nitrobenz amide 
N,N-Diisobutyl-m-nitrobenz amide 
N,N-Diisopropyl-m-nitrobenz amide 
N,N-Dimethyl-m-nitrobenz amide 
N,N-Dipropyl-m-nitrobenz amide 
N-Isobutyl-m-nitrobenz amide 
N-Isopropyl-m-nitrobenz amide 
1 -m-Nitrobenzoylpiperidine 
m-Nitro-N-propylbenzamide 



-3- 



Table 1. --Toxicity to house flies of space sprays containing certain 
benzamides in mixtures with 0.5 mg. of allethrin per milliliter. 
Concentration is 20 mg. per ml. unless otherwise indicated. 



Material 



Allethrin 
equivalent 
of mixture 



Allethrin equivalent 
required to show 
synergism 



Benzamide, N-amyl-m-nitro- 
N-benzyl-m-nitro- 
N-butyl-m-nitro- 
N - sec - butyl - m - nit ro - 
N-cyclohexyl-m-nitro- 
N,N-dibutyl-m-nitro- 
N,N-dicyclohexyl-m-nitro- 
N,N-diethyl-m-nitro- 
N,N-diisobutyl-m-nitro- 
N,N-diisopropyl-m-nitro- 
N,N- dimethykm-nitro- 
N, N-dipropyl-m -nitro- 
ns -isobutyl-m-nitro - 
N-isopropyl-m-nitro- 
N-methyl-m-nitro-i/ 
m-nitro-N- propyl - 

Benzanilide, 2'-chloro-3-nitro- 
3'-chloro-3-nitro- 
3-nitro- 

Hydrazine, 2 -m-nitrobenzoyl-1 -phenyl - 

Morpholine, 4-m-nitrobenzoyl- 

Piperidine, 1-m-nitrobenzoyl 



0.678 


0.731 


.509 


.731 


.563 


.797 


.420 


.797 


.600 


.631 


>1.5 


.797 


.619 


.631 


.665 


.610 


.995 


.631 


>1.5 


.797 


.654 


.610 


>1.5 


.797 


1.003 


.797 


.726 


.610 


.515 


.610 


.666 


.610 


.542 


.631 


.435 


.631 


.570 


.631 


.357 


.731 


.526 


.731 


.690 


.610 



1/ 10 mg. per ml. 



UNIVERSITY OF FLORIDA 
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